Addition of lithioimidazoles to isocyanates followed by Pd-coupling: Access to 4-substituted imidazole-2,5-dicarboxamides

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1869-1872

  Chittiboyina, Amar G ^a   Reddy, Ch Raji ^a   Watkins, E Blake ^a   Avery, Mitchell A ^a  

^a NONE

Author keywords

Imidazoles; Isocyanates; Lithiation; Palladium coupling

Indexed keywords

AMIDE; IMIDAZOLE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; LITHIUM DERIVATIVE; PALLADIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; LITHIATION; SUBSTITUTION REACTION;

EID: 1242293816     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.020     Document Type: Article

References (42)

1. Middlemiss D., Watson S.P. Tetrahedron. 50:1994;13049.
2. Bohem J.C., Gleason J.G., Pendrak I., Sarau H.M., Schmidt D.B., Foley J.J., Kingsbury W.D. J. Med. Chem. 36:1993;3333.
3. Walker R.P., Faulkner D.J., Van Engen D., Clardy J. J. Am. Chem. Soc. 103:1981;6772.
4. Holler T.P., Ruan F., Spaltenstein A., Hopkins P.B. J. Org. Chem. 54:1989;4570.
5. Lowe P.R., Sansom C.E., Schwalbe C.H., Stevens M.F.G., Clark A.S. J. Med. Chem. 35:1992;3377.
6. Commercon A., Paris J.M. Tetrahedron Lett. 32:1991;4905.
7. Hagedorn A.A. III, Erhardt P.W., Luma W.C., Wohl R.A., Cantor E., Chou Y.-L., Ingebretsen W.R., Lampe J.W., Pang D., Pease C.A., Wiggins J. J. Med. Chem. 30:1987;1342.
8. Carmely S., Ilan M., Kashman Y. Tetrahedron. 45:1989;2193.
9. Crawford D.J.K., Maddocks J.L., Jones D.N., Szawlowski P. J. Med. Chem. 39:1996;2690.
10. Tomioka H., Yano T., Takeda Y., Takeda H., Hirata N. Agric. Biol. Chem. 55:1991;1601.
11. Thurkauf A., Yuan J., Chen X., He X.S., Wasley J.W.F., Hutchison A., Woodruff K.H., Meade R., Hoffman D.C., Donovan H., Hohnes-Hertzog D.K. J. Med. Chem. 40:1997;1.
12. Baures P.W. Org. Lett. 1:1999;249.
13. Borodkin Y.S., Shabanov P.D., Lapina I.A., Yaitchnikov I.K. Activ. Nerv. Sup. 26:1984;97.
14. Bogdanova N.A., Kulikova O.G., Borodkin Y.S. Bull. Exp. Biol. Med. 111:1992;159.
15. Yasuda N., Iwagami H., Nakanishi E., Nakamiya T., Sasaki Y., Murata T.J. Antibiotics. 36:1983;242.
16. Vostrova L.N., Grenaderova M.V., Nedzvetsky V.S., Konup I.P., Andreyeva E.K., Bonder A.E. Khim.-Farm. Zh. 23:1989;584.
17. Wiznycia A.V., Baures P.W. J. Org. Chem. 67:2002;7151. and references cited therein.
18. Papadopoulos E.P. J. Org. Chem. 42:1977;3925.
19. Fukumoto Y., Sawada K., Hagihara M., Chatani N., Murai S. Angew. Chem. Int., Ed. 41:2002;2779.
20. Jutzi P., Sakriss W. Chem. Ber. 106:1973;2815.
21. Carpenter A.J., Chadwick D.J., Ngochindo R.I. J. Chem. Res. (S). 1983;196. and J. Chem. Res. (M). 1983;1913.
22. Katritzky A.R., Slawinski J.J., Brunner F. J. Chem. Soc., Perkin Trans. 1. 1989;1139.
23. Carver D.S., Lindell S.D., Stones E.A.S. Tetrahedron. 53:1997;14481.
24. Iddon B., Petersen A.K., Becher J., Christensen N.J. J. Chem. Soc., Perkin Trans. 1. 1995;1475. and references cited therein.
25. Groziak M.P., Wei L. J. Org. Chem. 56:1991;4296.
26. Carpenter A.J., Chadwick D.J. Tetrahedron. 42:1986;2351.
27. Shapiro G., Marzi M. Tetrahedron Lett. 34:1993;3401.
28. Revesz L., DiPadova F.E., Buhl T., Feifel R., Gram H., Hiestand P., Manning U., Romain W., Zimmerlin A.G. Bioorg. Med. Chem. Lett. 12:2002;2109.
29. Jetter M.C., Reitz A.B. Synthesis. 1998;829.
30. Benhida R., Lezama R., Fourrey J.L. Tetrahedron Lett. 39:1998;5963.
31. Revesz L., Bonne F., Makavou P. Tetrahedron Lett. 39:1998;5171.
32. Kawasaki I., Yamashita M., Ohta S. Chem. Pharm. Bull. 44:1996;1831.
33. Wang D., Haseltine J. J. Heterocycl. Chem. 31:1994;1637.
34. Kawasaki I., Yamashita M., Ohta S. J. Chem. Soc., Chem. Commun. 1994;2085.
35. Tsuji J. Perspectives in Organopalladium Chemistry for the 21st Century. 1999;Elsevier, Amsterdam.
36. Tsuji J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis. 1995;Wiley, Chichester, UK.
37. Bumagin N.A., Bykov V.V. Tetrahedron. 53:1997;14437. and references cited therein.
38. Frank W.C., Kim Y.C., Heck R.F. J. Org. Chem. 43:1978;2947.
39. Bach T., Krüger L. Eur. J. Org. Chem. 1999;2045.
40. Karig G., Spencer J.A., Gallagher T. Org. Lett. 3:2001;835.
41. Kim G., Kang S., Ryu Y., Keum G., Seo M.J. Synth. Commun. 29:1999;507.
42. +, found: 432.3264.